Podcast Summary: BigDeal Episode - "$250 Million Founder: What I Did Wrong & How To BUILD BIG | Ankur Nagpal"
Host: Codie Sanchez
Guest: Ankur Nagpal, CEO and Founder of Carrie, Former Founder of Teachable
Release Date: March 19, 2025
Introduction
In this episode of BigDeal, host Codie Sanchez welcomes Ankur Nagpal, an accomplished entrepreneur who has founded and sold a company for $250 million and is currently building another promising venture. Codie highlights Ankur's journey from humble beginnings in India and Oman to significant success in the U.S., emphasizing his ability to create impactful businesses twice over.
Early Entrepreneurship and Facebook Apps
[00:19] Ankur Nagpal:
Ankur recounts his entrepreneurial spirit that ignited in college, where he launched various side businesses, notably building Facebook apps that generated substantial revenue. By the age of 21, he had amassed a million dollars, leveraging viral marketing techniques.
[07:05] Ankur Nagpal:
"At our peak, we had more traffic than LinkedIn, Yelp, about the same as New York Times. We had like 4 or 5 million teenagers using it every single day." [07:20]
These early ventures taught him invaluable lessons in viral growth and scalable marketing strategies, setting the foundation for his future endeavors.
Founding and Growing Teachable
[27:43] Ankur Nagpal:
Ankur discusses the genesis of Teachable, born out of his experience teaching on platforms like Udemy and General Assembly. The key differentiator was immediate market pull, leading to steady growth from $3,000 in sales to $50 million in annual revenue within a few months.
Team Management and Culture:
[02:01] Cody Sanchez:
"I don't know. 35. Full time? Ish."
[02:08] Ankur Nagpal:
Ankur reflects on optimal team sizes, noting that Teachable thrived with around 50 employees but began feeling less enjoyable once the team exceeded 100.
[03:07] Ankur Nagpal:
He highlights challenges faced during the COVID-19 pandemic, including shifts in employee mindset and increased demands for workplace improvements, which diverted focus from business growth.
Selling Teachable During Market Crash
[51:10] Cody Sanchez:
Ankur shares the experience of selling Teachable during the unprecedented market drop caused by the onset of COVID-19.
[52:05] Ankur Nagpal:
"We ended up signing the deal to sell the company on the single biggest drop in market history." [00:00]
Despite the turbulent market conditions, Teachable continued to perform strongly, doubling its revenue shortly after the sale, showcasing resilience and growth potential even in adverse environments.
Building Carrie: Current Venture
[27:43] Ankur Nagpal:
Transitioning to his current venture, Carrie, Ankur outlines the company's focus on personal finance and tax optimization for small business owners. With over $2 million in annualized revenue and $100 million in customer assets, Carrie aims to compete with established financial giants like Vanguard, Schwab, and Fidelity.
Key Strategies:
-
Regulatory Compliance:
Ankur emphasizes the importance of regulatory moats, stating, "Regulatory stuff is one of the shittiest moats, but it's a strong moat." [66:55] -
Domain Name Investment:
The significant investment in the domain carrie.com underscores the strategic importance of trust and brand recognition in financial services.
Fundraising Strategies and Advice
[14:22] Ankur Nagpal:
Ankur reveals his unconventional approach to fundraising, successfully raising $70 million through Twitter DMs. He attributes this success to having "real skin in the game," where he offered zero management fees and committed a quarter of the capital himself.
Notable Quote:
"What worked for me was I had real fucking skin in the game." [15:07]
He advises aspiring entrepreneurs to persistently reach out, suggesting, "the first seven emails you send, the chances of getting a response are the same, which means you should send seven emails." [19:57]
Hiring and Team Management
[61:38] Ankur Nagpal:
Ankur shares insights on distinguishing A players from B and C players. He emphasizes the importance of hiring for initiative and speed, stating, "An A player is someone that I don't have to give initiative to. I don't have to tell them what to do." [63:18]
Strategies:
-
Contractual Trials:
Preferring to have potential hires work as contractors first to assess performance before full-time commitment. -
Diversity in Skills:
Valuing diverse competitive interests beyond just entrepreneurship, allowing for a more dynamic and engaging team environment.
Personal Life and Values
Ankur discusses the importance of family and personal experiences in shaping his entrepreneurial journey. He shares heartfelt stories about taking his parents on memorable vacations, highlighting his gratitude and the joy these experiences bring.
[10:21] Ankur Nagpal:
"We stay in nicer places than they have ever experienced. I get to see them experience all these things for the first time ever." [10:21]
He also touches upon his aspiration to buy a cricket team, blending his entrepreneurial drive with personal passions.
Advice for Aspiring Entrepreneurs
Ankur provides actionable advice for budding entrepreneurs:
-
Start with Zero Capital:
"If you want to put 20 or $30,000, you could get started." [16:28] -
Focus on Execution Over Perfection:
Encouraging a "done is better than perfect" mindset to overcome analysis paralysis. -
Build for Yourself:
Advocating for solving personal pain points to ensure product-market fit and easier customer acquisition.
Notable Quote:
"There's nothing like actually going out and doing it." [76:35]
Thoughts on Online Education
Reflecting on his experience with Teachable, Ankur critiques the current state of online education as being a mere replication of traditional formats. He envisions a future where online education is rebuilt to be digitally native, offering more interactive and engaging learning experiences.
[57:15] Ankur Nagpal:
"At some point, the way online education works, we're going to look back on what it is today and laugh." [57:15]
Mental Health in Startups and Fear of Failure
Ankur openly discusses the heightened fear of failure as a second-time founder, given his established reputation. He underscores the importance of resilience and the understanding that building a successful product remains a formidable challenge.
[39:56] Ankur Nagpal:
"I have a stronger fear of failure because I've built up this self image of myself as someone that is good at companies." [39:56]
Final Thoughts and Closing Remarks
Concluding the episode, Ankur emphasizes the essence of creation and execution over mere consumption. He encourages listeners to take actionable steps towards building something meaningful, reiterating the importance of persistence and practical learning.
[76:35] Ankur Nagpal:
"There's nothing like actually going out and doing it." [76:35]
[77:28] Ankur Nagpal:
"Even though it may seem like it the time, there's no amount of time that you will spend with your parents that you will ever regret when you get older." [77:28]
Notable Quotes with Timestamps
-
Ankur Nagpal:
"We ended up signing the deal to sell the company on the single biggest drop in market history." [00:00] -
Codie Sanchez:
"You are a BigDeal to us." [00:19] -
Ankur Nagpal:
"At our peak, we had more traffic than LinkedIn, Yelp, about the same as New York Times." [07:20] -
Ankur Nagpal:
"What worked for me was I had real fucking skin in the game." [15:07] -
Ankur Nagpal:
"There's nothing like actually going out and doing it." [76:35] -
Ankur Nagpal:
"Even though it may seem like it the time, there's no amount of time that you will spend with your parents that you will ever regret when you get older." [77:28]
Conclusion
This episode offers a deep dive into Ankur Nagpal's entrepreneurial journey, providing listeners with rich insights into building and scaling businesses, effective fundraising strategies, team management, and personal growth. Ankur's candid discussions and actionable advice make this episode a valuable resource for aspiring entrepreneurs aiming to make a significant impact.